CN109970680A - A kind of orange light material with AIE performance and its application in light conversion film - Google Patents
A kind of orange light material with AIE performance and its application in light conversion film Download PDFInfo
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- CN109970680A CN109970680A CN201711454464.XA CN201711454464A CN109970680A CN 109970680 A CN109970680 A CN 109970680A CN 201711454464 A CN201711454464 A CN 201711454464A CN 109970680 A CN109970680 A CN 109970680A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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Abstract
The present invention relates to a kind of orange light material with AIE performance and its applications in light conversion film.Orange light material of the invention, has a structure of chemical formula (I): (I) wherein R1- R7It is independently selected from hydrogen, C1-C8 alkyl, C1-C8 alkoxyl or halogen, C2-C8 replaces or unsubstituted allylic alkylation or alkynes alkyl, the aryl of C6-C30, C6-C30 aryl.The experimental results showed that having good absorption to background blue light (λ max=450nm) with film prepared by the compound of the present invention；The film that solid is made shows very strong fluorescent orange, has typical AIE property；Quantum yield of the compound 1 in PMMA film reaches 62%, and the quantum yield in solid film has reached 85%.Therefore gathering induced luminescence material of the invention can be applied in light conversion film, also potential to be applied to field of flat panel displays.
Description
Technical field
The present invention relates to the novel organic color conversion membrane materials shown for plane, and in particular to one kind contains benzo thiophene two
Azoles and tetraphenyl ethylene group, the orange light dyestuff with aggregation-induced emission property, are made film by solution spin coating, can be applied to
Plane is shown.
Background technique
With the continuous development of flat panel display, market to the growing of its demand, flat-panel monitor is small and exquisite with its,
It is light, energy saving, radiation it is small, Electro Magnetic Compatibility is good the advantages that, become the mainstream of 21 century display technology.Flat-panel monitor at
Color mode plays very crucial effect in its production process, its superiority and inferiority directly determines the colour rendering of flat-panel monitor
Can, service life and production cost.
Flat-panel monitor realizes that the major technique of full-color display is to pass through red, green, blue three primary colours using printing technology at present
Fluorescent material prepares device, still, since the aging variation degree of fluorescent material with three basic colour is larger, it is easy to cause colored display
There is color offset in device.Moreover, the manufacture craft of three primary colours device is more complex, it is at high cost.Through research after a period of time, people
Propose the new thinking of one kind to carry out the conversion of color, i.e., " color-by blue ".Indigo plant of this technology only with single high brightness
For color fluorophor as backlight, blue light becomes feux rouges and green light after color conversion coatings film, is formed together three with Blue backlight
Primary colours, to realize full-color display.This technology greatly simplifies the production technology of flat-panel monitor, also significantly increases aobvious
Show the stability of device, production cost also results in control.Can be used for color conversion coatings film material be broadly divided into it is organic and inorganic
Two classes.It has been investigated that organic transition material can have higher color conversion efficiency, color is also more saturated, so as to reality
Existing broader colour gamut.Meanwhile organic transition material is also more cheap, is easier to produce in enormous quantities, moreover it is possible to the modification of molecule is carried out to it,
To obtain better effect.
The application of organic fluorescence color conversion coatings film is usually to solidify the organic fluorescent dye of different colours by UV UV,
Or the modes such as heat cure are evenly distributed in macromolecular solid body thin film, then are excited by the Blue backlight of high brightness,
Therefore dye molecule realizes that color is converted to feux rouges and green light, is formed together three primary colours with background blue light, to realize electricity
The full-color display of electroluminescence device.
However, conventionally used organic dye molecule when concentration is higher, is easy to happen aggregation and leads to fluorescent quenching,
It hardly shines when filminess, therefore, in these conversion films, the concentration of organic molecule only has some thousandths of mostly, extremely low
Concentration often lead to film and light can not be fully absorbed, in order to improve efficiency the thickness for having to be significantly increased entire panel.
Hereafter, professor Tang Benzhong proposes the concept of aggregation-induced emission (AIE), this types of molecules uses diazosulfide
It is the molecule of unit with tetraphenyl ethylene, is widely used in ion detection, biological fluorescent labeling, OLED luminescent layer material for a long time
Material etc., however its application in organic light transform film is but rarely reported.
Summary of the invention
The invention reside in providing a kind of novel aggregation inducing material based on diazosulfide and tetraphenyl ethylene unit, and
The material is applied to organic light transform film.
A kind of orange light material with AIE performance has the structure of chemical formula (I):
Wherein R1- R7It is independently selected from hydrogen, C1-C8 alkyl, C1-C8 alkoxyl or halogen, C2-C8 substitution or unsubstituted
Allylic alkylation or alkynes alkyl, the aryl of C6-C30, C6-C30 aryl.
It is preferred that: R3、R4For hydrogen.
It is preferred that:
It is preferred that: R1、R2It is independently selected from hydrogen, C1-C8 alkyl, C1-C8 alkoxyl or halogen, C2-C8 substitution or unsubstituted
Allylic alkylation or alkynes alkyl, aryl, the aryl of C6-C30；
R6、R7It is independently selected from C1-C8 alkyl, the aryl of C6-C30, C6-C30 aryl.
It is preferred that having structure:
Preferably, R1、R2It is independently selected from hydrogen, C1-C4 alkyl, the aryl of C6-C20, C6-C20 aryl；
It is highly preferred that R1、R2It is identical；
It is further preferred: R1、R2Selected from hydrogen, tert-butyl, phenyl.
As mentioned above, compound described in formula of the invention (I) is as follows, but is not limited to cited structure:
It is preferred that: compound represented by formula (I) is with flowering structure
The experimental results showed that having very well with film prepared by the compound of the present invention to background blue light (λ max=450nm)
Absorption；The film that solid is made shows very strong fluorescent orange, has typical AIE property；Compound 1 is thin in PMMA
Quantum yield in film reaches 62%, and the quantum yield in solid film has reached 85%.Therefore aggregation inducing of the invention
Luminescent material can be applied in light conversion film, also potential to be applied to field of flat panel displays.
Detailed description of the invention
Ultraviolet-ray visible absorbing of Fig. 1 orange light dye composition 1 in toluene solution, PMMA film, solid film state (swashs
Hair wavelength is 450nm),
Fluorescence emission spectrum of Fig. 2 orange light dye composition 1 in toluene solution, PMMA film, solid film state,
The film with a thickness of 1-100um.
Specific embodiment
In order to describe the present invention in more detail, spy lifts following example, and but not limited to this.
Embodiment 1
The synthetic route of compound 1
The synthesis of compound 1b
Under nitrogen protection, by compound a (1.47g, 5mmol) (bibliography J.Polymer., 2010, vol.51, #
26p.6123-6131 synthesis), compound 1a (3.13g, 5.5mmol) (commercially available), Pd (PPh3)4(104mg, 0.1mmol), three uncles
Butyl phosphine (40mg, 10%), K2CO3250ml reaction flask is added in (3.04g, 22mmol), toluene (50ml) and water (10ml)
In.Nitrogen purge 3 times, 100 DEG C are heated to, keeps temperature, is reacted 12 hours, TLC detection compound a fully reacting.Stop
It only heats, is cooled to 20 DEG C, reaction solution is poured into water, ethyl acetate (250ml*2) extracts liquid separation, merges organic layer, with nothing
Evaporated under reduced pressure after aqueous sodium persulfate is dry, crude product obtain light yellow solid 1b (2.6g, yield 79%) after column chromatographs, MS (ESI):
m/z:657.3(M+)
The synthesis of compound 1
Under nitrogen protection, by compound 1b (2.5g, 3.8mmol), compound 1c (1.6g, 4.5mmol) (commercially available), Pd
(PPh3)4(104mg, 0.1mmol), tri-tert-butylphosphine (40mg, 10%), K2CO3(3.04g, 22mmol), toluene (50ml) and
Water (10ml) is added in 250ml reaction flask.Nitrogen purge 3 times, 100 DEG C are heated to, keeps temperature, is reacted 12 hours,
TLC detection compound a fully reacting.Stop heating, is cooled to 20 DEG C, reaction solution is poured into water, ethyl acetate (250ml*2)
Liquid separation is extracted, organic layer is merged, with evaporated under reduced pressure after anhydrous sodium sulfate drying, crude product obtains orange/yellow solid after column chromatographs
(1.8g, yield 58%), MS (ESI): m/z:822.1 (M+)。
Embodiment 2
The photophysical property of compound 1 is tested；
The photophysical property test of compound 1 is dissolved in toluene, solution concentration 1x10-5mol/L；Based on chemical combination
The PMMA film of object 1 is that the PMMA of dyestuff and corresponding proportion is dissolved in toluene, spin-coated and then drying preparation；The solid of dyestuff is thin
Film is that dyestuff is dissolved in THF, dries preparation after spin-coated；Have with film prepared by dyestuff to background blue light (λ max=450nm)
Good absorption (such as Fig. 1).The film that solid is made shows very strong fluorescent orange (such as Fig. 2), has typical AIE
Matter；Quantum yield of the compound 1 in PMMA film reaches 62%, and the quantum yield in solid film has reached 85%.
The photophysical property of the novel orange light dye composition 1 of the design synthesis of table 1
Claims (12)
1. a kind of orange light material with AIE performance has the structure of chemical formula (I):
Wherein R1- R7It is independently selected from hydrogen, C1-C8 alkyl, C1-C8 alkoxyl or halogen, C2-C8 replaces or unsubstituted alkene alkane
Base or alkynes alkyl, the aryl of C6-C30, C6-C30 aryl.
2. orange light material according to claim 1, in which: R3、R4For hydrogen.
3. orange light material according to claim 1 has the structure of chemical formula (II):
4. orange light material according to claim 3, in which: R1、R2Be independently selected from hydrogen, C1-C8 alkyl, C1-C8 alkoxyl or
Halogen, C2-C8 substitution or unsubstituted allylic alkylation or alkynes alkyl, aryl, the aryl of C6-C30；R6、R7It is independently selected from C1-
C8 alkyl, the aryl of C6-C30, C6-C30 aryl.
5. orange light material according to claim 4 has the structure of chemical formula (III):
6. orange light material according to claim 5, in which: R1、R2It is independently selected from hydrogen, C1-C4 alkyl, the aryl of C6-C20,
C6-C20 aryl.
7. orange light material according to claim 6, in which: R1、R2It is identical.
8. orange light material according to claim 7, in which: R1、R2Selected from hydrogen, tert-butyl, phenyl.
9. orange light material according to claim 5, with one in having structure:
10. orange light material according to claim 9 is following compounds:
11. application of any orange light material of claim 1-10 in light conversion film.
12. application according to claim 11, the light conversion film is applied to flat-panel monitor, organic electroluminescence
Part, mechanoluminescence device, organic field effect tube, in organic solar batteries and chemical sensor.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201711454464.XA CN109970680A (en) | 2017-12-28 | 2017-12-28 | A kind of orange light material with AIE performance and its application in light conversion film |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110828670A (en) * | 2019-11-28 | 2020-02-21 | 华南理工大学 | Multiplication type organic photoelectric detector based on AIE material and preparation method |
| CN113185477A (en) * | 2021-04-15 | 2021-07-30 | 西安交通大学 | Organic light-emitting nanocrystalline material and preparation method thereof |
| CN114085195A (en) * | 2021-11-30 | 2022-02-25 | 浙江播下环保科技有限公司 | Biodegradable film material with light conversion function, preparation method thereof and film doping material thereof |
| CN114106015A (en) * | 2021-10-11 | 2022-03-01 | 深圳大学 | Novel near-infrared two-region emission aggregation-induced luminescent material, and preparation method and application thereof |
| CN114621159A (en) * | 2022-04-06 | 2022-06-14 | 电子科技大学 | Diazosulfide-based fluorescent material, fluorescent polymer, fluorescent nanoparticles, and preparation method and application thereof |
-
2017
- 2017-12-28 CN CN201711454464.XA patent/CN109970680A/en not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| THAKSEN JADHAV ET AL: "Multi-Stimuli Responsive Donor−Acceptor Tetraphenylethylene Substituted Benzothiadiazoles", 《JOURNAL OF PHYSICAL CHEMISTRY C 》 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110828670A (en) * | 2019-11-28 | 2020-02-21 | 华南理工大学 | Multiplication type organic photoelectric detector based on AIE material and preparation method |
| CN110828670B (en) * | 2019-11-28 | 2021-03-30 | 华南理工大学 | Multiplication type organic photoelectric detector based on AIE material and preparation method |
| CN113185477A (en) * | 2021-04-15 | 2021-07-30 | 西安交通大学 | Organic light-emitting nanocrystalline material and preparation method thereof |
| CN114106015A (en) * | 2021-10-11 | 2022-03-01 | 深圳大学 | Novel near-infrared two-region emission aggregation-induced luminescent material, and preparation method and application thereof |
| CN114085195A (en) * | 2021-11-30 | 2022-02-25 | 浙江播下环保科技有限公司 | Biodegradable film material with light conversion function, preparation method thereof and film doping material thereof |
| CN114085195B (en) * | 2021-11-30 | 2022-06-14 | 浙江播下环保科技有限公司 | Biodegradable film material with light conversion function, preparation method thereof and film doping material thereof |
| CN114621159A (en) * | 2022-04-06 | 2022-06-14 | 电子科技大学 | Diazosulfide-based fluorescent material, fluorescent polymer, fluorescent nanoparticles, and preparation method and application thereof |
| CN114621159B (en) * | 2022-04-06 | 2023-04-18 | 电子科技大学 | Diazosulfide-based fluorescent material, fluorescent polymer, fluorescent nanoparticles, and preparation method and application thereof |
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Application publication date: 20190705 |